Abstract
The trifluoromethylation of iodoarenes was accomplished by use of a 2-trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition of the iodoarene to the Cu(I)–CF3 species is the rate-determining step.
Highlights
The introduction of a trifluoromethyl group is one of the most attractive reactions in drug discovery [1,2]
We have recently reported the trifluoromethylation of iodoarenes by use of 2-aryl-2-trifluoromethylbenzimidazoline as the trifluoromethylating reagent in the presence of 3 equiv of a copper salt [22]
The trifluoromethylation of p-iodonitrobenzene proceeded by use of 2-phenyl-2-trifluoromethyl-1-methylbenzimidazoline in the presence of catalytic amounts of CuI and 2,2’-bipyridyl as ligand
Summary
The introduction of a trifluoromethyl group is one of the most attractive reactions in drug discovery [1,2]. CuCF3 is a useful species for the trifluoromethylation of aryl halides and there are a number of precursors of CuCF3 for trifluoromethylation reactions. We report a catalytic trifluoromethylation of iodoarenes by use of benzimidazoline derivatives in the presence of a catalytic amount of copper salts and a bipyridyl ligand (Figure 1c). We first investigated the reaction conditions by use of p-iodonitrobenzene (1a) and 2-phenyl-2-trifluoromethyl-1methylbenzimidazoline (2) (Table 1).
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